1. Field of the Invention
The invention herein concerns novel 5-benzoyl-7-halo-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids and the pharmaceutically acceptable, non-toxic esters and salts thereof which are useful in the treatment of inflammation, pain and/or pyrexia in mammals, as platelet aggregation inhibitors and fibrinolytic agents, and as smooth muscle relaxants.
Said compounds and the corresponding 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids are prepared by decarboxylation of the respective corresponding 1,1 dicarboxylates.
Some of the 5-benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids, further discussed hereinbelow, and which are prepared by the process described herein, are similarly useful and are novel.
2. Prior Art
5-Benzoyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids, and their preparation by a synthetic route different from that disclosed herein, have been described in U.S. Pat. No. 4,089,969 and in U.S. Applications Nos. 71,443, now U.S. Pat. No. 4,232,038, and 71,444, now abandoned both filed Aug. 31, 1979. In these compounds, the benzoyl moiety is optionally substituted with lower alkyl, lower alkoxyl, fluoro, chloro or bromo or with alkylthio or alkylsulfinyl. Related 5-aroyl-1,2-dihydro-3H-pyrrolo[1,2-a]pyrrole-1-carboxylic acids and their pharmaceutically acceptable non-toxic esters and salts are described in U.S. Pat. Nos. 4,087,539 and 4,097,579. The corresponding 1-cyano compounds are described in U.S. Pat. No. 4,140,698. The corresponding 6-halo compounds are described in U.S. Application Ser. No. 157,719 filed June 9, 1980.